Dimethylformamide → HCID 59756815, compound

HRID 1663331Notes

Reaction equation

HRID 1663331 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:21])([C:14]2[C:15](Br)=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:52]=[O:53]>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:14]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[C:52](=[O:53])[O:21]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 59756817HCID 59756817, compound

Product 1

HCID 59756815HCID 59756815, compoundYield 43%

Conditions

Temperature
80 °C

Procedure

A mixture of 3.4 g (9.7 mmol) 1′-benzyl-2-bromo-2′,3′,5′,6′-tetrahydro-1′H-[3,4′]bipyridinyl-4′-ol, 3.3 ml (1.9 mmol) N,N-diisopropylethylamine, 0.22 g (1.0 mmol) Pd(II) acetate and 0.25 g (1.0 mmol) triphenylphosphine in 100 ml N,N-dimethylformamide was purged with carbon monoxide and stirred under an atmosphere of carbon monoxide at 80° C. for 72 h. The reaction mixture was diluted with tert-butyl methyl ether and washed with water (pH adjusted to 8 with saturated aqueous sodium bicarbonate solution). The aqueous layer was extracted with two portions of tert-butyl methyl ether. The combined organic layers were washed with two portions of water and brine, dried over sodium sulfate and concentrated to dryness. Flash-chromatography gave the title compound (1.2 g, 43%) as a yellow solid.

Workup

  1. customwas purged with carbon monoxide
  2. additionThe reaction mixture was diluted with tert-butyl methyl ether
  3. washwashed with water (
  4. extractionThe aqueous layer was extracted with two portions of tert-butyl methyl ether
  5. washThe combined organic layers were washed with two portions of water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a27577129cb449bebfd6e8ca1e8ff66c
Source dataset
uspto-grants-2011_10
Patent number
US08034937B2

Reaction notes

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