Water → [2-Amino-6-[2-(hydroxymethyl)phenyl]quinazolin-4-yl]isoindolin-2-ylmethanone

HRID 1631102ノート

反応式

HRID 1631102 の反応式
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](I)[CH:8]=2)[N:3]=1.[OH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.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]>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[CH2:25][OH:24])[CH:8]=2)[N:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 58457195(2-Amino-6-iodoquinazolin-4-yl)isoindolin-2-ylmethanone

生成物 1

HCID 56943443[2-Amino-6-[2-(hydroxymethyl)phenyl]quinazolin-4-yl]isoindolin-2-ylmethanone

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
130 °C

実験手順

100 mg of (2-amino-6-iodoquinazolin-4-yl)-(1,3-dihydroisoindol-2-yl)methanone are dissolved in 2 ml of ethylene glycol dimethyl ether. 48 mg of 2-hydroxymethylphenylboronic acid, 66 mg of potassium carbonate, 14 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride and 50 μl of water are added to this solution, and the mixture is heated at 130° C. under argon for 30 min. The hot mixture is filtered off through Celite, and the solution is evaporated to dryness under reduced pressure. The reddish residue obtained is triturated with acetonitrile, during which a beige solid precipitates out. This is filtered, washed with acetonitrile and dried overnight at 40° C. in a drying cabinet.

後処理

  1. filtrationThe hot mixture is filtered off through Celite
  2. customthe solution is evaporated to dryness under reduced pressure
  3. customThe reddish residue obtained
  4. customis triturated with acetonitrile, during which a beige solid
  5. customprecipitates out
  6. filtrationThis is filtered
  7. washwashed with acetonitrile
  8. customdried overnight at 40° C. in a drying cabinet

出典と根拠

ORDレコード
ord-9d9d96fadb784e3c8e0e917edd1a3463
出典データセット
uspto-grants-2014_07
特許番号
US08791129B2

反応ノート

読み込み中…