Potassium Carbonate → Ethyl 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423289노트

반응식

HRID 423289 반응식
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[NH:26][CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C=O)C>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[N:26]([CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionate2회HCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

생성물 1

HCID 59318376Ethyl 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

D2 (100 mg) was dissolved in DMF (1.2 ml), treated with K2CO3 (50 mg) then ethyl 3-bromopropionate (90 mg) and heated to 130° C. overnight. After this time LCMS showed the reaction to be incomplete so further ethyl 3-bromopropionate was added (45 mg) and stirring continued at 130° C. for 2 hours. LCMS showed no change so the reaction mixture was evaporated then partitioned between DCM and H2O. The organic layer was removed and the aqueous solution extracted with DCM. The combined organics were dried over MgSO4, filtered and evaporated to give the crude product (148 mg). This was purified on a silica cartridge (25+S), eluting with a 0 to 25% mixture of EtOAc in petroleum ether and then again on a 25+M cartridge with a 0 to 30% mixture of EtOAc in petroleum ether to give the title compound MF105672-144A3 (38 mg) as a white solid. δH (CDCl3, 400 MHz): 1.21 (3H, t), 2.85 (2H, t), 4.12 (2H, q), 4.50 (2H, t), 6.60 (1H, d), 7.21 (1H, d), 7.42-7.52 (6H, m), 7.91 (1H, s), 8.00 (1H, d), 8.46 (1H, s). MS (ES+): C26H20F3N3O3S requires 511; found 512 (MH+).

후처리

  1. customthe reaction
  2. additionwas added (45 mg)
  3. customwas evaporated
  4. customthen partitioned between DCM and H2O
  5. customThe organic layer was removed
  6. extractionthe aqueous solution extracted with DCM
  7. dry with materialThe combined organics were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give the crude product (148 mg)
  11. customThis was purified on a silica cartridge (25+S)
  12. washeluting with a 0 to 25% mixture of EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-be0c302d0e244d2bbff54eb7a8ee8e99
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101775B2

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