Dimethylformamide → 10-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575184노트

반응식

HRID 575184 반응식
[Br:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13](I)[N:14]=[C:7]3[C:6]=2[CH:16]=1.C[Si](N[Si](C)(C)C)(C)C.C[N:28](C)[CH:29]=[O:30]>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>[Br:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:29]([NH2:28])=[O:30])[N:14]=[C:7]3[C:6]=2[CH:16]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 13838HexamethyldisilazaneHCID 6831272510-Bromo-9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

생성물 1

HCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide수율 55%

시약·촉매·용매 1

HCID 178418807HCID 178418807, 화합물촉매

반응 조건

온도
70 °C

실험 절차

Similar to as described in Example 10, A suspension of 10-bromo-9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (16.0 g, 39.12 mmol, 1.00 equiv)(US2012/245144A1), HMDS (19.3 g, 119.88 mmol, 3.06 equiv) and Pd(dppf)Cl2 CH2Cl2 (1.6 g, 1.95 mmol, 0.05 equiv) in N,N-dimethylformamide (240 mL) was stirred for 2 h at 70° C. under a carbon monoxide atmosphere (1 atm). After cooling to room temperature the reaction was quenched by addition of methanol (5 mL), diluted by ethyl acetate (1 L), washed with water (200×4 mL) and brine (200 mL), dried over sodium sulfate, and concentrated under vacuum. The residue was further purified by FC(Silica and ethyl acetate/petroether 2:1) to give 7.0 g (55%) of the titled compound as a grey solid.

후처리

  1. temperatureAfter cooling to room temperature the reaction
  2. customwas quenched by addition of methanol (5 mL)
  3. additiondiluted by ethyl acetate (1 L)
  4. washwashed with water (200×4 mL) and brine (200 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was further purified by FC(Silica and ethyl acetate/petroether 2:1)

출처 및 근거

ORD 기록
ord-2b646a4c911543769d8ce93216730eed
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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