Sodium t-butoxide → HCID 86712751, compound

HRID 1754544Notes

Reaction equation

HRID 1754544 reaction equation
Cl[C:2]1[C:7]2[N:8]([C:20]([C@H:22]3[CH2:26][CH2:25][CH2:24][NH:23]3)=[O:21])[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C1C=CC=CC=1C1C(N(C)C)=CC=CC=1)(C)(C)C>[O:21]=[C:20]1[N:8]2[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C:6]3[C:7]2=[C:2]([CH:3]=[CH:4][CH:5]=3)[N:23]2[CH2:24][CH2:25][CH2:26][C@H:22]12

Participants

6

Reactant 2

HCID 23676156Sodium t-butoxideHCID 86712752HCID 86712752, compound

Product 1

HCID 86712751HCID 86712751, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 27349362-Di-tert-butylphosphino-2'-(N,N-dimethylamino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

65 mg of (R)-tert-butyl 9-chloro-1-(pyrrolidine-2-carbonyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate was stirred together with 1.8 mg of 2′-(ditert-butylphosphino)-N,N-dimethylbiphenyl-2-amine, 2.5 mg Pd2(dba)3 and 19 mg sodium 2-methylpropan-2-olate at 100° C. over 10 hours in toluene. The reaction mixture was then cooled to room temperature and evaporated. The residue was purified by column chromatography on silica (eluent: 10-25% ethyl acetate in heptane) to yield 20 mg of the title compound as a beige solid.

Workup

  1. customevaporated
  2. customThe residue was purified by column chromatography on silica (eluent: 10-25% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-0943d68180b9434cb8f3ea95aece0e68
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

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