Lithium Chloride → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-5-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879354노트

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HRID 879354 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:27]([CH3:28])=[CH:26][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21](Cl)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:36][N:37]1[C:45]2[C:40](=[N:41][C:42]([Sn](CCCC)(CCCC)CCCC)=[CH:43][CH:44]=2)[CH:39]=[N:38]1.[Cl-].[Li+]>[Cu]I.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>[C:1]([O:5][C@@H:6]([C:12]1[C:27]([CH3:28])=[CH:26][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:42]4[N:41]=[C:40]5[CH:39]=[N:38][N:37]([CH3:36])[C:45]5=[CH:44][CH:43]=4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetateHCID 867001551-methyl-5-(tributylstannyl)-1H-pyrazolo[4,3-b]pyridine

생성물 1

HCID 86700154(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-pyrazolo[4,3-b]pyridin-5-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
120 °C

실험 절차

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (48 mg, 0.091 mmol) in microwave vial, was added 1-methyl-5-(tributylstannyl)-1H-pyrazolo[4,3-b]pyridine (47 mg, 0.111 mmol), copper(I) iodide (9 mg, 0.045 mmol), lithium chloride (11 mg, 0.27 mmol), Pd(PPh3)4 (10 mg, 0.009 mmol). The reaction mixture was heated at 120° C. for 4 hours. Then the mixture was washed by saturated NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down, purified by silica gel column, eluting by 0-60% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C34H32ClN5O3S: 626.2 (M+H+); found: 626.3.

후처리

  1. washThen the mixture was washed by saturated NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated down
  6. custompurified by silica gel column
  7. washeluting by 0-60% EtOAc in hexanes
  8. customto give the product

출처 및 근거

ORD 기록
ord-eec5377f94c244d6babdc0ab779651a7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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