Triethylamine → HCID 67019901, compound

HRID 1673238Notes

Reaction equation

HRID 1673238 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[O:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]([NH2:18])[C:11]3=[CH:10][C:9]=2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:4]([Cl:28])[CH:3]=1.[C:29](Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].CCN(CC)CC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[O:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]([NH:18][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:11]3=[CH:10][C:9]=2[C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[C:4]([Cl:28])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67019926HCID 67019926, compound

Product 1

HCID 67019901HCID 67019901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 7-(4-bromo-2-chlorophenyl)-6-(4-chlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-amine (536.2 mg, 1.12 mmol) in 10 mL of CH2Cl2 at 0° C. was added pivaloyl chloride (166 μL, 1.34 mmol) and NEt3 (313 μL, 2.24 mmol). After stirring at rt for 1 h, the reaction mixture was concentrated. Chromatography on a Biotage 40+M cartridge using 1:3 v/v EtOAc/hexanes as the eluant afforded the product: 1H NMR δ 1.26 (s, 9H), 1.47 (s, 3H), 1.55 (s, 3H), 1.82 (t, J=12.3, 1H), 2.26 (dd, J=6.2, 13.3, 1H), 5.48 (m, 1H), 5.81 (br. s, 1H), 6.97 (d, J=8.5, 2H), 7.16-7.20 (m, 3H), 7.33-7.42 (m, 2H), 7.55 (s, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customafforded the product

Sources & evidence

ORD record
ord-4f48f1d894b246098a8e95cd9ee7bac3
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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