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

HRID 606314ノート

反応式

HRID 606314 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-87572e2fb1c248c6a992207cef683825
出典データセット
uspto-grants-2011_03
特許番号
US07915288B2

反応ノート

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