Boron tribromide → HCID 136041870, 화합물

HRID 1466555노트

반응식

HRID 1466555 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26]C)=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH3:25])[N:9]=2)[CH:7]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:26])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH3:25])[N:9]=2)[CH:7]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 49856845HCID 49856845, 화합물

생성물 1

HCID 136041870HCID 136041870, 화합물수율 34.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (145 mg, 0.379 mmol, 1 eq) in 3.0 mL dichloromethane was added boron tribromide (1.1 mL of a 1.0 M solution in dichloromethane, 1.1 mmol, 2.9 eq). The reaction was stirred at room temperature for 16 hours. The reaction mixture was then quenched with methanol, diluted into ethyl acetate, and washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resulting solid material was triturated with 2 mL DMSO, and the solids collected and dried under vacuum to yield 47.8 mg (34%) of N-(3-(5-chloro-2-hydroxyphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=369.0; 1H NMR (400 MHz, DMSO-d6) δ: 10.45 (s, 1H), 9.99 (s, 1H), 9.33 (d, 1H), 8.76 (d, 1H), 8.65 (s, 1H), 8.27 (s, 1H), 7.45 (s, 1H), 7.30 (m, 2H), 7.08 (d, 1H), 3.92 (s, 3H).

후처리

  1. customThe reaction mixture was then quenched with methanol
  2. additiondiluted into ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting solid material was triturated with 2 mL DMSO
  7. customthe solids collected
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-6c3e5d09c96f4c74b38da7347dc72111
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999998B2

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