Water → Tert-butyl 4-[4-[5-amino-6-[2-(3-hydroxyphenyl)ethynyl]pyrazin-2-yl]phenyl]sulfonylpiperidine-1-carboxylate

HRID 869040노트

반응식

HRID 869040 반응식
[NH2:1][C:2]1[C:3]([C:9]#[C:10][C:11]2[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=2)=[N:4][C:5](Br)=[CH:6][N:7]=1.CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]3)(=[O:34])=[O:33])=[CH:28][CH:27]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CC#N.CCOC(C)=O.Cl.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH:35]3[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:39][CH2:40]3)(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[N:4][C:3]=1[C:9]#[C:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 67481388tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)phenylsulfonyl)piperidine-1-carboxylateHCID 86667832HCID 86667832, 화합물

생성물 1

HCID 67478804Tert-butyl 4-[4-[5-amino-6-[2-(3-hydroxyphenyl)ethynyl]pyrazin-2-yl]phenyl]sulfonylpiperidine-1-carboxylate

시약·촉매·용매 4

HCID 178418851HCID 178418851, 화합물촉매HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

3-[2-(3-Amino-6-bromo-pyrazin-2-yl)ethynyl]phenol (100 mg, 0.3447 mmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonylpiperidine-1-carboxylate (186.7 mg, 0.4136 mmol) and K3PO4 (146.3 mg, 0.6894 mmol) were combined in MeCN (2 mL)/water (0.5 mL) and Pd[P(tBu)3]2 (8.811 mg, 0.01724 mmol) was added. The reaction was heated at 60° C. for 15 hours. The reaction was cooled to ambient temperature and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The material was used directly in the next step without further purification.

후처리

  1. additionwas added
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (×3)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material was used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-2f8ab5622bf0406daf579a61bcf8ebcf
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969356B2

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