Benzothiazole-6-carbonitrile → tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174088노트

반응식

HRID 2174088 반응식
[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1)#[N:2].CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.[CH:32]([C:34]1[C:42]([O:43][CH3:44])=[CH:41][C:40]([CH3:45])=[C:39]2[C:35]=1[CH:36]=[CH:37][N:38]2[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:33]>C1COCC1.[Li+].CC([N-]C(C)C)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[C:8]([CH:32]([OH:33])[C:34]3[C:42]([O:43][CH3:44])=[CH:41][C:40]([CH3:45])=[C:39]4[C:35]=3[CH:36]=[CH:37][N:38]4[C:46]([O:48][C:49]([CH3:51])([CH3:50])[CH3:52])=[O:47])[S:9][C:5]=2[CH:4]=1)#[N:2]

참가 물질

6

반응물 3

HCID 10607144Benzothiazole-6-carbonitrileHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

생성물 1

HCID 86701724tert-Butyl 4-((6-cyanobenzo[d]thiazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 2724682Lithium diisopropylamide용매

실험 절차

To a solution of 6-cyanobenzothiazol (CAS #:58249-61-9) (54.60 mg, 0.341 mmol) in THF (1.06 mL), LDA in Heptane/THF/Ethylbenzene (205 uL, 0.409 mmol) was added at −78° C. After 20 mins, a solution of tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (79 mg, 0.273 mmol) in THF (1.68 mL) was added to the reaction mixture at −78° C. After stirring for 1.5 h, the reaction was quenched with MeOH, sat. aq. NH4Cl solution and brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, concentrated, and purified using FCC eluting with Heptane/EtOAc to provide the title compound. MS (ESI−) m/z 448 (M−H).

후처리

  1. customthe reaction was quenched with MeOH, sat. aq. NH4Cl solution and brine
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified
  8. washeluting with Heptane/EtOAc

출처 및 근거

ORD 기록
ord-babb7957472c46a49844c1d1331221d8
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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