Sodium Carbonate → HCID 54527580, compound

HRID 1856699Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[OH:7][C@H:8]([CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[C@H:9]([CH3:20])[O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.Br[C:30]1[S:34][C:33]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:32][CH:31]=1>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>[OH:7][C@H:8]([CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[C@H:9]([CH3:20])[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:30]2[S:34][C:33]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:32][CH:31]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2M Aqueous sodium carbonate (0.75 ml), (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (Example 21a)), 0.19 g), and tetrakis(triphenylphosphine)palladium(0) (0.025 g) were added to a solution of 5-bromothiophene-2-sulfonic acid amide (0.242 g) in ethanol (2 ml). The mixture was heated at 90° C. for 2 hours. The mixture was cooled to room temperature and the solvents were evaporated under reduced pressure. The reaction mixture was triturated with acetone (10 ml) and filtered through a short silica gel column. The column was eluted with acetone and the resulting filtrate evaporated to give the title compound as a solid (0.064 g).

Workup

temperatureThe mixture was cooled to room temperature
customthe solvents were evaporated under reduced pressure
customThe reaction mixture was triturated with acetone (10 ml)
filtrationfiltered through a short silica gel column
washThe column was eluted with acetone
customthe resulting filtrate evaporated

Sources & evidence

ORD record: ord-49ab3a927eb44fb69a7b6b3d0757fd65
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143751

Reaction notes

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