Sodium Carbonate → 2-(3',4'-Difluorophenyl)-5-bromopyrimidine

HRID 1603296Notes

Reaction equation

HRID 1603296 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[F:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[F:16].C(=O)([O-])[O-].[Na+].[Na+].FC1C(F)=C(OCCCCCCCC)C=CC=1C1N=CC(Br)=CN=1>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.COCCOC>[F:9][C:10]1[CH:11]=[C:12]([C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH:13]=[CH:14][C:15]=1[F:16]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 542039742-(3',4'-Difluorophenyl)-5-bromopyrimidineYield 98.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (3.84 g, 14.9 mmol), 3,4-difluorophenylboronic acid (3.06 g, 19.4 mmol), tetrakis(triphenylphosphine)palladium (344 mg, 0.30 mmol), DME (50 ml), aqueous 2M sodium carbonate (50 ml). The experimental procedure was as described for compound 4. The crude product was purified by flash chromatography (5% ethyl acetate-light petroleum) to give the difluorophenylpyrimidine 12 (3.97 g, 75%) (from MeOH), m.p. 148° C.; νmax /cm-1 1610, 1530, 1435s, 1330, 1270, 790 and 780; δ 7.26(1H, m, 5'-H), 8.17-8.30(2H, m, 2' and 6'-H) and 8.82 (2H, s,4- and 6-H); m/z 272 (M+), 270 (M+), 164 and 139.

Workup

  1. customThe crude product was purified by flash chromatography (5% ethyl acetate-light petroleum)

Sources & evidence

ORD record
ord-a021e79bafac4d2a8e002017a4e1ff0f
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

Loading…