Tributylphosphine → 5-(1-Isopropyl-piperidin-4-yloxy)-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic Acid 1-tert-butyl Ester 2-ethyl Ester

HRID 1437707노트

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HRID 1437707 반응식
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]2=[N:10][CH:11]=[C:12]([OH:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5].[CH:23]([N:26]1[CH2:31][CH2:30][CH:29](O)[CH2:28][CH2:27]1)([CH3:25])[CH3:24].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:15]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:9]2=[N:10][CH:11]=[C:12]([O:14][CH:29]3[CH2:30][CH2:31][N:26]([CH:23]([CH3:25])[CH3:24])[CH2:27][CH2:28]3)[CH:13]=[C:8]2[CH:7]=1)=[O:5]

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 796811-Isopropylpiperidin-4-olHCID 684243571H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 2-ethyl ester

생성물 1

HCID 684233285-(1-Isopropyl-piperidin-4-yloxy)-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic Acid 1-tert-butyl Ester 2-ethyl Ester수율 21%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To the turbid solution of 0.2 g (0.65 mmol) 5-hydroxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (as prepared in WO 05/000849) and 1-isopropyl-piperidin-4-ol (commercially available) in 6 ml tetrahydrofuran, 0.26 g (1.3 mmol) tributylphosphine were added and the mixture was cooled to 0° C. Within 60 min. 32.9 mg (1.3 mmol) 1,1′-(azodicarbonyl)dipiperidine were added under stirring and the reaction was allowed to reach room temperature. After 19 hours the brown suspension was filtered and evaporated. The residue was stirred in tert butyl methyl ether, filtered and the clear filtrate was evaporated and flash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) to give 60 mg (21%) of the product as a yellow oil.

후처리

  1. customto reach room temperature
  2. filtrationAfter 19 hours the brown suspension was filtered
  3. customevaporated
  4. stirringThe residue was stirred in tert butyl methyl ether
  5. filtrationfiltered
  6. customthe clear filtrate was evaporated
  7. customflash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v)

출처 및 근거

ORD 기록
ord-7910e3945a734c7283a50cfbfc0bd7b1
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622466B2

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