tert-butyl rac-(3R,4R)-4-(6-bromo-4-oxobenzo[h]quinazolin-3(4H)-yl)-3-hydroxypiperidine-1-carboxylate → HCID 86666963, compound

HRID 82472Notes

Reaction equation

HRID 82472 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]=[CH:7][N:6]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]1[OH:29])[C:5]2=[O:30].[Cl-].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][Zn+])=[CH:35][N:34]=1>ClCCl.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>[Cl:32][C:33]1[N:34]=[CH:35][C:36]([CH2:39][C:2]2[CH:3]=[C:4]3[C:9](=[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=24)[N:8]=[CH:7][N:6]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH:17]2[OH:29])[C:5]3=[O:30])=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 67970513tert-butyl rac-(3R,4R)-4-(6-bromo-4-oxobenzo[h]quinazolin-3(4H)-yl)-3-hydroxypiperidine-1-carboxylateHCID 178478124HCID 178478124, compound

Product 1

HCID 86666963HCID 86666963, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a dry 25 mL round bottom flask containing tert-butyl rac-(3R,4R)-4-(6-bromo-4-oxobenzo[h]quinazolin-3(4H)-yl)-3-hydroxypiperidine-1-carboxylate (0.163 g, 0.344 mmol) under N2(g) was added (2-chloro-5-pyridyl)methylzinc chloride (0.5 M in THF, 2.06 mL, 1.03 mmol) and tetrakis(triphenylphosphine)palladium (0) (10 mol %). The reaction was heated to reflux at 90° C. for 20 h, cooled to room temperature, and diluted with dichloromethane. Hexanes were added to the solution and the resultant beige precipitate was collected via filtration, washed with dichloromethane and hexanes, and dried on high vac to provide crude tert-butyl rac-(3R,4R)-4-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3(4H)-yl]-3-hydroxypiperidine-1-carboxylate that gave a mass ion (ES+) of 520.9 for M+H+.

Workup

  1. temperatureThe reaction was heated
  2. temperaturecooled to room temperature
  3. filtrationthe resultant beige precipitate was collected via filtration
  4. washwashed with dichloromethane and hexanes
  5. customdried on high vac

Sources & evidence

ORD record
ord-244360d416fe4d0990d7f7d7f4146bc2
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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