Boron tribromide → 6-hydroxy-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinoline-4-carbaldehyde

HRID 606314

반응식

HRID 606314 반응식
B(Br)(Br)Br.[CH:5]([C:8]1[C:9]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27]C)=[CH:24][CH:25]=3)[C:20]([CH:29]=[O:30])=[C:19]([CH3:31])[N:18]=2)=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2)([CH3:7])[CH3:6]>C(Cl)Cl>[OH:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[C:17]([C:9]1[C:8]([CH:5]([CH3:7])[CH3:6])=[CH:16][CH:15]=[C:14]3[C:10]=1[CH:11]=[N:12][NH:13]3)=[N:18][C:19]([CH3:31])=[C:20]2[CH:29]=[O:30]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 866159341-(5-isopropyl-1H-indazol-4-yl)-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde

생성물 1

HCID 1363416606-hydroxy-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinoline-4-carbaldehyde수율 34.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

BBr3 (8.8 g, 35 mmol) is added slowly to a solution of 1-(5-Isopropyl-1H-indazol-4-yl)-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde (842 mg, 2.3 mmol) in DCM (15 ml) at −78° C. The cold bath is removed and the mixture is warmed to room temperature, and then stirred for a further 1 h. The reaction mixture is poured into ice-water mixture and treated with NH4OH (6 ml). The layers are separated and the aqueous layer is extracted with DCM. The combined organic layers are dried (Na2SO4) and evaporated. The residue is chromatographed on silica gel eluting with EtOAc/MeOH (20:1) to give 490 mg of starting material and 276 mg of 6-hydroxy-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinoline-4-carbaldehyde. 1H NMR (CDCl3) 10.9 (s, 1H), 8.87 (s, 1H), 7.62-7.42 (m, 4H), 6.99 (d, 1H), 3.09 (s, 3H), 2.73-2.67 (m, 1H), 1.23 (d, 3H), 1.12 (d, 3H).

후처리

  1. customThe cold bath is removed
  2. additionThe reaction mixture is poured into ice-water mixture
  3. additiontreated with NH4OH (6 ml)
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with DCM
  6. dry with materialThe combined organic layers are dried (Na2SO4)
  7. customevaporated
  8. customThe residue is chromatographed on silica gel eluting with EtOAc/MeOH (20:1)

출처 및 근거

ORD 기록
ord-87572e2fb1c248c6a992207cef683825
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915288B2

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