Ethanol → HCID 178491788, compound

HRID 589691Notes

Reaction equation

HRID 589691 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[NH:21][N:20]=[N:19][N:18]=3)[CH:12]=2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[F:22][C:23]1[CH:24]=[CH:25][C:26]([O:32][CH3:33])=[C:27](B(O)O)[CH:28]=1.C([O-])(O)=O.[Na+].CCO>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.O>[F:22][C:23]1[CH:28]=[CH:27][C:26]([O:32][CH3:33])=[C:25]([C:2]2[S:6][C:5]([S:7]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[NH:21][N:20]=[N:19][N:18]=4)[CH:12]=3)(=[O:9])=[O:8])=[CH:4][CH:3]=2)[CH:24]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 178527479HCID 178527479, compound2×

Product 1

HCID 178491788HCID 178491788, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-N-[3-(1H-tetrazol-5-yl)phenyl]thiophene-2-sulfonamide (Intermediate 17) (19 mg, 0.05 mmol), 5-fluoro-2-methoxyphenylboronic acid (10 mg, 0.06 mmol), Pd(PPh3)4 (3 mg, 0.0025 mmol), NaHCO3 (13 mg, 0.15 mmol), EtOH (750 μL) and water (250 μL) was heated in a sealed tube at 80° C. over night. The mixture was concentrated and purified by preparative HPLC (ACE C8 5 μm, 0.1% TFA in water/CH3CN) giving 4.1 mg (19%) of the title compound. MS (ESI+) calcd for C18H14FN5O3S2 431.052209, found 431.051439.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC (ACE C8 5 μm, 0.1% TFA in water/CH3CN)

Sources & evidence

ORD record
ord-09592182a6584d649d60035e56d64a87
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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