1,3-Difluoroacetone → HCID 56591410, compound

HRID 706931Notes

Reaction equation

HRID 706931 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([O:10][C:11]3[CH:37]=[C:36]([N:38]4[CH2:43][CH2:42][N:41]([CH2:44][C:45]5[CH2:50][CH2:49][C:48]([CH3:52])([CH3:51])[CH2:47][C:46]=5[C:53]5[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=5)[CH2:40][CH2:39]4)[CH:35]=[CH:34][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]4[CH2:30][NH:29][CH2:28]4)=[C:21]([N+:31]([O-:33])=[O:32])[CH:20]=3)(=[O:18])=[O:17])=[O:14])[CH:9]=[C:4]2[CH:3]=[CH:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:74][CH2:75][C:76](=O)[CH2:77][F:78]>ClCCl>[Cl:59][C:56]1[CH:55]=[CH:54][C:53]([C:46]2[CH2:47][C:48]([CH3:52])([CH3:51])[CH2:49][CH2:50][C:45]=2[CH2:44][N:41]2[CH2:42][CH2:43][N:38]([C:36]3[CH:35]=[CH:34][C:12]([C:13]([NH:15][S:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]5[CH2:30][N:29]([CH:76]([CH2:77][F:78])[CH2:75][F:74])[CH2:28]5)=[C:21]([N+:31]([O-:33])=[O:32])[CH:20]=4)(=[O:18])=[O:17])=[O:14])=[C:11]([O:10][C:8]4[CH:9]=[C:4]5[CH:3]=[CH:2][NH:1][C:5]5=[N:6][CH:7]=4)[CH:37]=3)[CH2:39][CH2:40]2)=[CH:58][CH:57]=1

Participants

5

Reactant 3

HCID 2283971,3-DifluoroacetoneHCID 5049666Sodium triacetoxyborohydrideHCID 67126462HCID 67126462, compound

Product 1

HCID 56591410HCID 56591410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 161B (0.118 g), sodium triacetoxyborohydride (0.035 g) and 1,3-difluoropropan-2-one (0.012 g) were stirred together in dichloromethane (1 mL) overnight. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL) and extracted into dichloromethane (30 mL). The organic layer was dried and concentrated. Silica gel chromatography (Reveleris 12 g) eluting with a gradient of 0.5% to 3.5% methanol/dichloromethane over 30 minutes (Flow=36 ml/min) gave the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 11.67 (s, 1H), 11.47-11.21 (m, 1H), 8.85 (s, 1H), 8.55 (d, 1H), 8.03 (d, 1H), 7.80 (dd, 1H), 7.54-7.45 (m, 3H), 7.33 (s, 2H), 7.04 (d, 3H), 6.67 (d, 1H), 6.38 (dd, 1H), 6.20 (d, 1H), 4.43 (dt, 4H), 3.56 (t, 2H), 3.46 (s, 2H), 3.12 (m, 6H), 2.74 (m, 3H), 2.17 (m, 7H), 1.95 (s, 2H), 1.39 (d, 2H), 0.92 (s, 6H).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution (10 mL)
  2. extractionextracted into dichloromethane (30 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. washSilica gel chromatography (Reveleris 12 g) eluting with a gradient of 0.5% to 3.5% methanol/dichloromethane over 30 minutes (Flow=36 ml/min)

Sources & evidence

ORD record
ord-574a660ed7b34f4b9dc0616b87706de7
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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