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

HRID 2079620Notes

Reaction equation

HRID 2079620 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8756415a21a742d1bd0526ede76d7254
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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