Sodium Carbonate → 3-[2-(2-Fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazolin-6-yl]-benzamide

HRID 2387260ノート

反応式

HRID 2387260 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:6]=[C:5]2[N:19]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH:21]=[CH:20]1.C(=O)([O-])[O-].[Na+].[Na+].B(O)(O)[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([NH2:43])=[O:42])[CH:36]=1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:7]1[N:6]=[C:5]([N:19]2[C:27]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[CH:21]=[CH:20]2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:35]3[CH:36]=[C:37]([CH:38]=[CH:39][CH:40]=3)[C:41]([NH2:43])=[O:42])[CH:3]=2)[N:8]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 103647546-Bromo-2-(2-fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline

生成物 1

HCID 184406453-[2-(2-Fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazolin-6-yl]-benzamide収率 26.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

6-Bromo-2-(2-fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline from Step E, Example 3 (0.1 g, 0.23 mmol) was dissolved in tetrahydrofuran (5 ml). Sodium carbonate (0.075 g, 0.7 mmol) and benzamide-3-boronic acid (0.040 g, 0.24 mmol) was added followed by tetrakis(triphenylphosphine)palladium(0) (0.005 g, 0.004 mmol) after degassing for 5 mins. Water (0.5 ml) was added drop wise and the mixture was magnetically stirred and heated to 80° C. for 4 hrs. Water was added and product extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated in a rotary evaporator and the residue further purified using a HPLC reverse phase column using an acetonitrile and water gradient containing 0.1% trifluoroacetic acid to yield the title compound (0.028 g, 25%). MS (ES) 460.0 (M+H)+

後処理

  1. customafter degassing for 5 mins
  2. additionWater (0.5 ml) was added drop wise
  3. additionWater was added
  4. extractionproduct extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. customevaporated in a rotary evaporator
  7. customthe residue further purified
  8. additioncontaining 0.1% trifluoroacetic acid

出典と根拠

ORDレコード
ord-3c53dc7ca21e4ecd915644a4f1bf646a
出典データセット
uspto-grants-2012_09
特許番号
US08268857B2

反応ノート

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