Water → methanesulfonic acid 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzo-furan-2-yl]-ethyl ester

HRID 2251125Notes

Reaction equation

HRID 2251125 reaction equation
[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:14]=[CH:15][C:16]4[O:20][C:19]([CH2:21][CH2:22][OH:23])=[CH:18][C:17]=4[CH:24]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].O>C(Cl)Cl>[N:1]1[N:12]2[C:4]([N:5]=[C:6]3[C:10](=[C:11]2[C:13]2[CH:14]=[CH:15][C:16]4[O:20][C:19]([CH2:21][CH2:22][O:23][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:18][C:17]=4[CH:24]=2)[CH2:9][CH2:8][CH2:7]3)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 585877152-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzofuran-2-yl]-ethanol

Product 1

HCID 58587719methanesulfonic acid 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzo-furan-2-yl]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzofuran-2-yl]-ethanol (200 mg, 0.91 mmol) in CH2Cl2 (10 ml) was added triethylamine (303 mg, 3 mmol) and methanesulfonyl chloride (525 mg, 4.56 mmol). The mixture was stirred at room temperature for 30 minutes. Water was added to the reaction and the organic layer separated. The aqueous layer was extracted with CH2Cl2 and the combined organic extracts were dried and concentrated to give methanesulfonic acid 2-[5-(6,7-dihydro-5H-1,4,8a-triaza-s-indacen-8-yl)-benzo-furan-2-yl]-ethyl ester, which was used in the next reaction without further purification.

Workup

  1. customthe organic layer separated
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. customthe combined organic extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7c85a14c8314be1b64f38645fc2f7f4
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

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