1,2-Dichloroethane → HCID 68109168, compound

HRID 2179354Notes

Reaction equation

HRID 2179354 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]3[C:16]4[CH2:17][NH:18][CH2:19][CH2:20][C:21]=4[O:22][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:39]CCCl>>[ClH:39].[CH3:25][N:18]1[CH2:19][CH2:20][C:21]2[O:22][C:12]3[CH:11]=[C:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH:15]=[CH:14][C:13]=3[C:16]=2[CH2:17]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68108586HCID 68108586, compound

Product 1

HCID 68109168HCID 68109168, compound

Procedure

To a solution of the product of Example 60, step E (15 mg, 0.05 mmol) in 1,2-dichloroethane (0.5 mL) was added formaldehyde (12 μL, 37% in water). The reaction mixture was stirred at ambient temperature for 10 min before sodium triacetoxyborohydride (61 mg, 0.29 mmol) was added. The reaction mixture was stirred for 15 h, quenched with saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with 1.25 M HCl in methanol and the resulting solution concentrated in vacuo to afford 2-methyl-7-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (9.5 mg, 61%, AUC HPLC 95.7%) as a white solid: mp 242-245° C.; 1H NMR (CD3OD, 300 MHz) δ 8.21-8.13 (m, 1H), 7.98 (d, J=7.2 Hz, 2H), 7.87 (dd, J=8.3 Hz, 1.2 Hz, 1H), 7.71 (d, J=8.1 Hz, 1H), 7.63-7.54 (m, 3H), 4.74-4.30 (br s, 2H), 3.96-3.60 (br s, 2H), 3.30 (br s, 2H), 3.13 (s, 3H); ESI MS m/z 328 [M+H]+.

Workup

  1. additionwas added
  2. customquenched with saturated sodium bicarbonate solution
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with 1.25 M HCl in methanol
  8. concentrationthe resulting solution concentrated in vacuo

Sources & evidence

ORD record
ord-1db39e1bcd7b4339a8e9afb9d2f06910
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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