tert-Butanol → HCID 22485087, compound

HRID 2181040Notes

Reaction equation

HRID 2181040 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][C:16]=3[Cl:27])[C:9]([O:11][CH2:12][CH3:13])=[N:10][C:5]2=[CH:4][CH:3]=1.[C:28]([OH:32])(C)(C)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:63]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[Cl:27][C:16]1[CH:17]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:20][C:15]=1[CH2:14][N:8]1[C:6]2=[N:7][C:2]([C:28]([OH:32])=[O:63])=[CH:3][CH:4]=[C:5]2[N:10]=[C:9]1[O:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 812191,3-Bis(diphenylphosphino)propaneHCID 22484970HCID 22484970, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 22485087HCID 22485087, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

5-Bromo-3-(2-chloro-4-phenylbenzyl)-2-ethoxy-3H-imidazo[4,5-b]pyridine (57 mg) was dissolved in N,N-dimethylformamide (1.3 ml) and tert-butyl alcohol (1.0 ml) and triethylamine (30.4 mg), 1,3-bis(diphenylphosphino)propane (17 mg) and palladium (II) acetate (9.3 mg) were successively added. The mixture was stirred under a 10 atm. carbon monoxide atmosphere at 85° C. for 48 hr. The insoluble matter was filtered off and washed with chloroform. The filtrate and washing were combined and concentrated to dryness under reduced pressure. The residue was purified by thin layer chromatography (chloroform:methanol=19:1) to give 3-(2-chloro-4-phenylbenzyl)-2-ethoxy-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (43 mg) as a brown oil.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. washwashed with chloroform
  3. washThe filtrate and washing
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by thin layer chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-376aaa05a5b643579dd8ce7ad6726459
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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