Sodium Carbonate → HCID 68509571, compound

HRID 1715352Notes

Reaction equation

HRID 1715352 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]([OH:12])[C:8]([F:11])([F:10])[F:9])[S:5][CH:6]=1.CC1(C)COB([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[N:23]3)OC1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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>[F:9][C:8]([F:11])([F:10])[CH:7]([C:4]1[S:5][CH:6]=[C:2]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[N:23]3)[CH:3]=1)[OH:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 53406992HCID 53406992, compoundHCID 57620096HCID 57620096, compound

Product 1

HCID 68509571HCID 68509571, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the alcohol (E1) (1.0 eq.) and the crude boronic ester (E2) (1.3 eq.) in DMF (1.0M), together with 2N Na2CO3 aqueous solution (2.0 eq.) was degassed with a stream of Ar for 10 min. Pd(PPh3)4 (0.05 eq) was added and the reaction heated overnight at 90° C. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica using 500% EtOAc/Petroleum ether to yield the desired compound as a power. 1H NMR (400 MHz, CDCl3, 300K) δ 8.81 (2H, m), 8.20 (1H, d, J=2.0 Hz), 8.10 (1H, d, J=8.8 Hz), 7.98 (1H, dd, J=8.8, 2.0 Hz), 7.68 (1H, s), 7.61 (1H, s), 5.38 (1H, q, J=6.4 Hz). MS (ES) C14H9F3N2OS requires: 310, found: 311 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica using 500% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-0fd1a462d97d4048a94258ae6fbdb028
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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