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

HRID 1954503Notes

Reaction equation

HRID 1954503 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-iodopyrimidine2×HCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 542039742-(3',4'-Difluorophenyl)-5-bromopyrimidineYield 75%

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; δ7.26 (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-b8cfef467f454cfebe192efd0f6478f4
Source dataset
uspto-grants-2000_09
Patent number
US06121448

Reaction notes

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