Triphenylphosphine → Tert-butyl 4-(7-bromo-2-chloroquinazolin-8-yloxy)piperidine-1-carboxylate

HRID 2079620노트

반응식

HRID 2079620 반응식
CCOC(/N=N/C(OCC)=O)=O.[Br:13][C:14]1[C:23]([OH:24])=[C:22]2[C:17]([CH:18]=[N:19][C:20]([Cl:25])=[N:21]2)=[CH:16][CH:15]=1.O[CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Br:13][C:14]1[C:23]([O:24][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[C:22]2[C:17]([CH:18]=[N:19][C:20]([Cl:25])=[N:21]2)=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 591992277-Bromo-2-chloroquinazolin-8-ol

생성물 1

HCID 59199246Tert-butyl 4-(7-bromo-2-chloroquinazolin-8-yloxy)piperidine-1-carboxylate수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of DEAD (404 mg, 2.32 mmole) in THF (0.5 mL) was added to a solution of 7-bromo-2-chloroquinazolin-8-ol (400 mg, 1.54 mmole), tert-butyl 4-hydroxypiperidine-1-carboxylate (621 mg, 3.09 mmole) and PPh3 (610 mg, 2.32 mmole) in THF (5.5 mL) at RT. After 1.5 hours, silica gel was added to the reaction which was evaporated to dryness and loaded onto a flash column. The product was eluted with 25% EtOAc/hexane to give tert-butyl 4-(7-bromo-2-chloroquinazolin-8-yloxy)piperidine-1-carboxylate in 80% yield (545 mg, 1.23 mmole).

후처리

  1. additionsilica gel was added to the reaction which
  2. customwas evaporated to dryness
  3. washThe product was eluted with 25% EtOAc/hexane

출처 및 근거

ORD 기록
ord-8756415a21a742d1bd0526ede76d7254
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932262B2

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