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Potassium Carbonate → (S)-ethyl 2-(2-(1H-benzo[d]imidazol-6-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate

HRID 879521
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인쇄 미리보기

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HRID 879521 반응식
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[NH:30]1[C:34]2[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:33]=2[N:32]=[CH:31]1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.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>[NH:30]1[C:34]2[CH:35]=[C:36]([C:2]3[S:3][C:4]4[C:10]([C:11]5[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=5)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=4[N:6]=3)[CH:37]=[CH:38][C:33]=2[N:32]=[CH:31]1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 17981796(1H-Benzo[d]imidazol-5-yl)boronic acidHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

생성물 1

HCID 86700341(S)-ethyl 2-(2-(1H-benzo[d]imidazol-6-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-(tert-butoxy)acetate

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A microwave vial was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (78 mg, 0.16 mmol), (1H-benzo[d]imidazol-6-yl)boronic acid (44 mg, 0.27 mmol), then Pd(PPh3)4 (22 mg, 0.02 mmol). The vial was flushed with argon, diluted with dioxane (1.5 mL) and to this was added 2M aqueous K2CO3 (0.25 mL, 0.5 mmol). The vial was sealed, heated to 100° C. for 2 hours, and then allowed to cool to room temperature. The mixture was diluted with EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-20% MeOH/CH2Cl2 gradient) to afford the desired product. LCMS-ESI+: calc'd for C29H29ClN3O3S: 534.2 (M+H+); Found: 534.3 (M+H+).

후처리

  1. customThe vial was flushed with argon
  2. additiondiluted with dioxane (1.5 mL)
  3. customThe vial was sealed
  4. temperatureto cool to room temperature
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica gel column chromatography (0-20% MeOH/CH2Cl2 gradient)

출처 및 근거

ORD 기록
ord-0588e08529384f46801b56d28bcff5e2
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987250B2

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