Isopropenyl chloroformate → prop-1-en-2-yl 2-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenylcarbamate

HRID 1098610노트

반응식

HRID 1098610 반응식
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:21].C([O-])(O)=O.[Na+].Cl[C:28]([O:30][C:31]([CH3:33])=[CH2:32])=[O:29]>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:21][C:28](=[O:29])[O:30][C:31]([CH3:33])=[CH2:32]

참가 물질

5

반응물 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 594583192-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzenamine

생성물 1

HCID 66729122prop-1-en-2-yl 2-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenylcarbamate수율 90%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of Example A1 (2.0 g, 7.04 mmol) and saturated aq NaHCO3 (100 mL) in EtOAc (100 mL) was cooled in an ice bath and treated with isopropenyl chloroformate (1.6 mL, 14.64 mmol). The reaction mixture was allowed to slowly warm to RT overnight. The organic layer was separated and washed with sat aq NaHCO3 (25 mL) and brine (25 mL), dried (MgSO4), concentrated in vacuo and re-crystallized (diethylether) to provide prop-1-en-2-yl 2-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenylcarbamate (2.32 g, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.69 (br s, 1 H), 8.38 (d, J=5.6 Hz, 1 H), 8.26 (s, 1 H), 7.96 (d, J=0.8 Hz, 1 H), 7.67 (br t, J=8.4 Hz, 1 H), 7.27 (d, J=2.4 Hz, 1 H), 7.22 (dd, J=11.2, 2.4 Hz, 1 H), 7.00 (m, 1 H), 6.69 (dd, J=5.6, 2.4 Hz, 1 H), 4.74 (m, 1 H), 4.72 (s, 1 H), 3.84 (s, 3 H), 1.92 (s, 3 H); MS (ESI) m/z: 369.1 (M+H+).

후처리

  1. customThe organic layer was separated
  2. washwashed with sat aq NaHCO3 (25 mL) and brine (25 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customre-crystallized (diethylether)

출처 및 근거

ORD 기록
ord-5d7ed1d91daa4b8a926c512daac763c4
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143293B2

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