Methanesulfonyl chloride → 6-(methylsulfonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

HRID 41883Notes

Reaction equation

HRID 41883 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]2[CH2:21][NH:22][CH2:23][C:16]=12>C(Cl)Cl>[CH3:1][S:2]([N:22]1[CH2:21][C:17]2[C:16](=[N:15][CH:20]=[CH:19][CH:18]=2)[CH2:23]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 15194166,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Product 1

HCID 592568296-(methylsulfonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.97 mL, 12.4 mmol) was added dropwise to a −10° C. solution of diisopropyl-ethylamine (5.16 mL, 31.1 mmol) and 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (2.0 g, 10.0 mmol) in CH2Cl2 (20 mL). The mixture was stirred overnight at rt diluted with CH2Cl2 (300 mL) and washed with saturated aqueous sodium bicarbonate. The organic phase was separated, dried (MgSO4) and filtered through a short silica gel pad with EtOAc rinse. The filtrate was concentrated to yield 2.15 g (quantitative) of Ex 10-Step 1 product as a solid which was used without further purification: LCMS m/z 199.2 (M+1); 1H NMR (400 MHz, CDCl3) δ 8.54 (d, J=4.9, 1H), 7.61 (d, J=7.8, 1H), 7.25 (dd, J=7.8, 5.1, 1H), 4.75 (AB quartet, JAB=2.1, ΔvAB=7.8, 4H), 2.94 (s, 3H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through a short silica gel pad with EtOAc
  5. washrinse
  6. concentrationThe filtrate was concentrated
  7. customto yield 2.15 g (quantitative) of Ex 10-Step 1 product as a solid which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-c5581c1d79fd4c6793b277c33d1b679b
Source dataset
uspto-grants-2013_09
Patent number
US08536164B2

Reaction notes

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