Sodium Carbonate → 3-fluoro-4-methyl-2'-(N-triphenylmethyl-1H-tetrazol-5-yl)biphenyl

HRID 1078034Notes

Reaction equation

HRID 1078034 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([F:9])[CH:3]=1.[C:10]1([C:16]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:17]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3B(O)O)=[N:20][N:19]=[N:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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.C1(C)C=CC=CC=1>[F:9][C:4]1[CH:3]=[C:2]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]2[N:17]([C:16]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:18]=[N:19][N:20]=2)[CH:7]=[CH:6][C:5]=1[CH3:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1710404-Bromo-2-fluorotolueneHCID 103427452-(1-Trityl-1H-tetrazol-5-YL)phenylboronic acid

Product 1

HCID 194304273-fluoro-4-methyl-2'-(N-triphenylmethyl-1H-tetrazol-5-yl)biphenyl

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

4-Bromo-2-fluorotoluene (5.00 g, 26 mmol, 1 eq), 2-(N-triphenylmethyl-1H-tetrazol-5-yl)benzeneboronic acid (U.S. Pat. No. 5,130,439) (14.29 g, 26 mmol, 1 eq), tetrakistriphenylphosphinepalladium (0) (1.53 g, 1.3 mmol, 0.05 eq), tetrabutylammonium bromide (0.42 g, 1.3 mmol, 0.05 eq), 2M sodium carbonate (28.99 mL, 58 mmol, 2.23 eq) and toluene (200 mL) were mixed and refluxed for 4 hours. The reaction was worked up as in example 1, part D to yield 11.98 g of an amber glass. The glass was dissolved in ethyl acetate (25 mL) and triturated with ether to yield 6.04 g of white solid product. The filtrate was concentrated and flash chromatographed in 9:1 hexanes/ethyl acetate to yield a further 3.72 g of white solid product. NMR (CDCl3) δ 8.00-7.85 (m, 1H); 7.55-7.40 (m, 2H); 7.40-7.10 (m, 10H); 7.00-6.70 (m, 9H); 2.18 (s, 3H). ##STR55##

Workup

  1. temperaturerefluxed for 4 hours

Sources & evidence

ORD record
ord-c5203e1bcb4f44d394e7b39c7b5bc994
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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