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

HRID 2387260노트

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HRID 2387260 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-3c53dc7ca21e4ecd915644a4f1bf646a
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268857B2

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