2-(Thiophen-2-yl)benzoyl chloride → HCID 90411877, compound

HRID 2175956Notes

Reaction equation

HRID 2175956 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH:10]2[CH2:15][CH:14]3[NH:16][CH:11]2[CH2:12][CH2:13]3)=[N:6][CH:7]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH:10]2[CH2:15][CH:14]3[N:16]([C:24]([C:23]4[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=4[C:18]4[S:17][CH:21]=[CH:20][CH:19]=4)=[O:25])[CH:11]2[CH2:12][CH2:13]3)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 27955572-(Thiophen-2-yl)benzoyl chlorideHCID 90412355HCID 90412355, compound

Product 1

HCID 90411877HCID 90411877, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To (±)-2-(((5-fluoropyridin-2-yl)oxy)methyl)-7-azabicyclo[2.2.1]heptane (35 mg, 0.2 mmol) in DCM (2.5 mL) was added TEA (25 μL, 0.2 mmol)) followed by 2-(thiophen-2-yl)benzoyl chloride (40 mg, 0.2 mmol) in DCM (2.5 mL). After 18 h, the reaction was diluted with DCM and washed with H2O. The aqueous layer was extracted DCM (1×). The combined organics were dried (Na2SO4). Purification via silica gel chromatography (50-100% EtOAc in hexanes) gave the title compound (37 mg, 57%). MS (ESI) mass calcd. for C23H21FN2O2S, 408.1; m/z found 409.1 [M+H]+.

Workup

  1. washwashed with H2O
  2. extractionThe aqueous layer was extracted DCM (1×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. customPurification via silica gel chromatography (50-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e6b0ba4502a6459ebee725233efb393d
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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