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Lithium diisopropylamide → HCID 178451568、化合物

HRID 1909064
ノート
印刷プレビュー

反応式

HRID 1909064 の反応式
[C:1]([Si:5]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]3[N:19](CN(C)C)[CH:20]=[N:21][C:16]3=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[C:38]([O:42][C:43]([N:45]1[C:49]2=[CH:50][N:51]=[CH:52][C:53]([C:54]3[CH:59]=[C:58]([C:60](OC)=[O:61])[CH:57]=[CH:56][C:55]=3[C:64]#[N:65])=[C:48]2[CH:47]=[CH:46]1)=[O:44])([CH3:41])([CH3:40])[CH3:39].[Li+].CC([N-]C(C)C)C>C1COCC1>[C:38]([O:42][C:43]([N:45]1[C:49]2=[CH:50][N:51]=[CH:52][C:53]([C:54]3[CH:59]=[C:58]([C:60]([C:20]4[NH:19][C:17]5=[N:18][C:13]([N:10]6[CH2:11][CH2:12][CH:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([C:26]7[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=7)[C:32]7[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=7)[CH2:8][CH2:9]6)=[CH:14][CH:15]=[C:16]5[N:21]=4)=[O:61])[CH:57]=[CH:56][C:55]=3[C:64]#[N:65])=[C:48]2[CH:47]=[CH:46]1)=[O:44])([CH3:41])([CH3:39])[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2724682Lithium diisopropylamideHCID 66599777HCID 66599777、化合物HCID 672864874-(2-Cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 178451568HCID 178451568、化合物収率 90.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of {5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-imidazo[4,5-b]pyridin-3-ylmethyl}-dimethyl-amine (574 mg, 1.12 mmol) and 4-(2-cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (474 mg, 1.26 mmol, 1.1 eq) (Step 1 example 140) in THF (0.1M), cooled to −78° C., was slowly added 1M LDA (2 mol eq). After 1 hr, the reaction mixture was quenched with 50% acetic acid in water (0.25 vols.) at −78° C. The mixture was allowed to warm to room temperature and concentrated to remove most THF. The residue was diluted with EtOAc (20 mL) and basified with aqueous ammonium hydroxide (30%) until pH>8. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was then purified by trituration from Acetonitrile affording 4-(5-{5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine-2-carbonyl}-2-cyano-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester as a red solid (900 mg, 1.01 mmol, 90%). MS ESI m/z 802.7 (M+H)+.

後処理

  1. customthe reaction mixture was quenched with 50% acetic acid in water (0.25 vols.) at −78° C
  2. concentrationconcentrated
  3. customto remove most THF
  4. additionThe residue was diluted with EtOAc (20 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by trituration from Acetonitrile

出典と根拠

ORDレコード
ord-57fbb9f259114cad8dda66771c4fffdc
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598217B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート