Sodium Iodide → HCID 17956117, compound

HRID 2103277Notes

Reaction equation

HRID 2103277 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([CH3:16])=[C:12]([F:15])[CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:17].[CH2:18]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH2:19][CH2:20][CH3:21].[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:18]([CH:22]1[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([CH3:16])=[C:12]([F:15])[CH:13]=3)[CH2:8][CH2:7][C:6]2=[O:17])[CH2:24][CH2:23]1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 132838674-ButylpiperidineHCID 17956066HCID 17956066, compound

Product 1

HCID 17956117HCID 17956117, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 4 mL vial was charged with 1-(3-chloropropyl)-7-fluoro-6-methyl-3,4-dihydro-1H-quinolin-2-one (112KK01) (0.047 g, 0.18 mmol), 4-butylpiperidine (0.039 g, 0.28 mmol), NaI (0.100 g, 0.67 mmol), and K2CO3 (0.075 g, 0.54 mmol) in MeCN (2 mL) and shaken at 50° for 20 h. The reaction mixture was quenched with water, and the product extracted into EtOAc. The combined organic layers were purified by cation exchange CC followed by purification by flash CC (SiO2; MeOH/DCM 1:10) to give the title compound (112KK06) (0.022 g, 34%). 1H NMR (CD3OD) δ 7.05 (d, J=8.4 Hz, 1H), 6.93 (d, J=11.7 Hz, 1H), 3.93 (t, J=7.2 Hz, CH2), 2.93 (d, J=11.1 Hz, 2H), 2.83 (t, J=6.9 Hz, CH2), 2.60-2.56 (m, 2H), 2.44-2.40 (m, 2H), 2.19 (D, J=1.8 Hz, CH3) 2.03-1.98 (m, 2H), 1.86-1.79 (m, 2H), 1.69 (d, J=11.0 Hz, 2H), 1.31-1.19 (m, 9H), 0.89 (t, J=6.6 Hz, CH3); 13C NMR (CD3OD) δ 172.4, 161.7 (d, J=241.0 Hz), 139.5 (d, J=10.0 Hz), 131.7 (d, J=6.1 Hz), 123.5 (d, J=3.6 Hz), 119.9 (d, J=17.4 Hz), 104.0 (d, J=28.1 Hz), 56.8, 55.0, 41.5, 37.3, 36.7, 33.0, 32.8, 30.1, 25.5, 25.3, 23.9, 14.4, 13.7.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe product extracted into EtOAc
  3. customThe combined organic layers were purified by cation exchange CC
  4. customfollowed by purification by flash CC (SiO2; MeOH/DCM 1:10)

Sources & evidence

ORD record
ord-a0c98b7a573044f68d8361d8bb40a3f9
Source dataset
uspto-grants-2009_08
Patent number
US07576100B2

Reaction notes

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