Sodium Carbonate → HCID 11336470, compound

HRID 2223781Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)#[N:18].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.[Pd]>[C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14]([OH:16])=[O:15])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)#[N:18]

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of [(4-bromophenyl)(methylsulfonyl)amino]acetic acid (intermediate 3, 20 mg, 65 μmol) in dimethoxyethane (1 mL) was added in one portion to a mixture of 4-cyanophenyl-boronic acid (9.5 mg, 65 μmol) and fibrecat FC1001 (2.71% Pd; 25 mg, 6.5 μmol) in a Smith microwave reaction vial. Aqueous sodium carbonate solution (1.0 M; 130 μL, 130 μmol) was added and the vial capped. The crude reaction mixture was heated at 150° C. for 15 min using a Smith Synthesiser microwave reactor. On cooling the vial was opened and the contents were filtered through a Whatman 5 μM filter tube, washing the filter cake with methanol (2×1 mL). The filtrate was evaporated and the resulting residue was purified using mass directed auto-preparative reverse phase HPLC to give the title compound (1.1 mg, 5%) as a white solid. LC/MS: 2.94 min; z/e 329, calcd (M−1) 329. 1H NMR (400 MHz: MeOD): 7.80 (4H), 7.75 (2H), 7.65 (2H), 4.45 (2H), 3.10 (3H).

Workup

customThe crude reaction mixture
temperatureOn cooling the
filtrationthe contents were filtered through a Whatman 5 μM
filtrationfilter tube
washwashing the filter cake with methanol (2×1 mL)
customThe filtrate was evaporated
customthe resulting residue was purified

Sources & evidence

ORD record: ord-098115e41ae54c2493eba67fdfc9d1b9
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375248B2

Reaction notes

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