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Sodium Carbonate → (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

HRID 1028060
ノート
印刷プレビュー

反応式

HRID 1028060 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:20]2)O1.[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44](Cl)[N:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[C:12]3[N:19]2[CH2:24][CH2:23][CH2:22][C@H:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:20]2)[N:43]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 151332374-(Benzyloxy)-2-chloropyrimidineHCID 67316377(S)-tert-butyl 1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

生成物 1

HCID 67338681(S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate収率 88%

試薬・触媒・溶媒 2

HCID 178418807
HCID 178418807、化合物
触媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of (S)-tert-butyl 1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (1.0 equiv.), 4-(benzyloxy)-2-chloropyrimidine (2.0 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv) in a 20 ml microwave vial, DME and 2M Na2CO3 were added (1.0 M). The vial was submitted to 125° C. for 20 min in microwave. The resulting mixture was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed with NaCl(sat.), dried over Na2SO4, concentrated and purified by reverse-phase HPLC to yield (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (88%). LC/MS=512.1 (M+H), LC=3.40 min.

後処理

  1. additionwere added (1.0 M)
  2. customThe resulting mixture was partitioned between EtOAc and H2O
  3. customUpon separation
  4. washthe organic layer was washed with NaCl(sat.)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by reverse-phase HPLC

出典と根拠

ORDレコード
ord-0b71be8b6bec49f38e28495a9ce11354
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08735424B2

反応ノート

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