Phenylboronic Acid → HCID 19799252, compound

HRID 2081209Notes

Reaction equation

HRID 2081209 reaction equation
Br[C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].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>[CH3:11][N:9]1[C:10]2[C:2]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:3][CH:4]=[CH:5][C:6]=2[C:7]2[C:15](=[O:16])[NH:14][CH2:13][CH2:12][C:8]1=2

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 15712506HCID 15712506, compound

Product 1

HCID 19799252HCID 19799252, compoundYield 90.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent2×

Procedure

A mixture of 6-bromo-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (200 mg), phenylboronic acid (131 mg), tetrakis(triphenylphosphine)palladium (0) (11 mg) and 2N sodium carbonate (5 ml) in DME (10 ml) was heated at reflux for 3 h. The cooled mixture was diluted with 2N sodium carbonate (50 ml) and extracted with dichloromethane (3 100 ml). The combined organic extracts were concentrated in vacuo and the residue was purified by FCC eluting with System A (100:8:1) to give a solid (180 mg) which was triturated with ether (20 ml) to give the title compound (160 mg), m.p. 242°-245°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. extractionextracted with dichloromethane (3 100 ml)
  4. concentrationThe combined organic extracts were concentrated in vacuo
  5. customthe residue was purified by FCC
  6. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-92d08e31cd124c84a8733e500192d496
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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