Triethylamine → HCID 69345138, compound

HRID 1948193Notes

Reaction equation

HRID 1948193 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([B:10]([OH:12])[OH:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CCN(CC)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([B:10]([OH:12])[OH:11])=[CH:3][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22832067(3-Amino-4-methoxyphenyl)boronic acid

Product 1

HCID 69345138HCID 69345138, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-amino-4-methoxyphenylboronic acid (1 eq, 2.10 mmol, 0.35 g) in CH2Cl2 (5 mL) at −78° C. was added Et3N (6 eq, 13.0 mmol, 1.7 mL). The reaction was stirred for 30 minutes then methanesulfonyl chloride (1.1 eq, 2.30 mmol, 0.26 g) was added. The reaction was then stirred at −78° C. for 1 hour. The reaction was allowed to warm to room temperature and diluted with CH2Cl2. The reaction washed with 1.0N aqueous HCl and the organic phase was extracted (×3). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure to afford 4-methoxy-3-(methylsulfonamido)phenylboronic acid (1.92 mmol, 0.49 g, 96%) as a white solid.

Workup

  1. stirringThe reaction was then stirred at −78° C. for 1 hour
  2. washThe reaction washed with 1.0N aqueous HCl
  3. extractionthe organic phase was extracted (×3)
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-637ea919d5fb45c3b8d714efc0c9621a
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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