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Triethylamine → tert-Butyl 16-oxo-15-{3-[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]prop-2-yn-1-yl}-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

HRID 1615853
ノート
印刷プレビュー

反応式

HRID 1615853 の反応式
[O:1]=[C:2]1[C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][C:4]2([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]1[CH2:25][C:26]#[CH:27].I[C:29]1[CH:30]=[C:31]2[C:44](=[CH:45][CH:46]=1)[CH2:43][C@:33]1([C:41]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]1=[O:42])[CH2:32]2.C(N(CC)CC)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[O:1]=[C:2]1[C:7]2([CH2:8][CH2:9][CH2:10][CH2:11]2)[N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:5][C:4]2([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N:3]1[CH2:25][C:26]#[C:27][C:29]1[CH:30]=[C:31]2[C:44](=[CH:45][CH:46]=1)[CH2:43][C@:33]1([C:41]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]1=[O:42])[CH2:32]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8471TriethylamineHCID 58118662(2R)-5-iodo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2 回HCID 58118691tert-Butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate2 回

生成物 1

HCID 66864621tert-Butyl 16-oxo-15-{3-[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]prop-2-yn-1-yl}-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A stirred suspension of tert-butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate (110 mg, 0.294 mmol, described in Intermediate 23), (2R)-5-iodo-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (106 mg, 0.294 mmol, described in Intermediate 27), tetrakis(triphenylphosphine)palladium(0) (34 mg, 0.029 mmol), copper(I)iodide (23 mg, 0.121 mmol), and triethylamine (0.082 mL, 0.588 mmol) in degassed DMF (1.5 mL) was heated at 50° C. for 30 min. The reaction was quenched with water (30 mL), partitioned with saturated NaHCO3 solution (30 mL) and extracted with EtOAc (2×60 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified on silica gel, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, to yield the title compound. MS: m/z=609 (M+1).

後処理

  1. customThe reaction was quenched with water (30 mL)
  2. custompartitioned with saturated NaHCO3 solution (30 mL)
  3. extractionextracted with EtOAc (2×60 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified on silica gel
  8. washeluting with a gradient of CH2Cl2

出典と根拠

ORDレコード
ord-49f50a7915e04da5b33884f9b81d94bb
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765759B2

反応ノート

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