Water → HCID 118566572, compound

HRID 1056777Notes

Reaction equation

HRID 1056777 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16](Cl)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.O1CCOCC1.O.[F-].[Cs+].[C:34]1(B2OC(C)(C)C(C)(C)O2)[CH2:38][CH2:37][CH2:36][CH:35]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([C:34]4[CH2:38][CH2:37][CH2:36][CH:35]=4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1185559652,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluorocyclohexylmethyl)-amide

Product 1

HCID 118566572HCID 118566572, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

2,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide (300 mg, 0.74 mmol, 1.00 eq) in 1,4-Dioxane (6 mL, 69.44 mmol, 20 V)/Water (2 mL, 111.02 mmol, 6.67 V) was taken in a microwave vial and to this were added Cesium fluoride (338.80 mg, 2.23 mmol, 3.00 eq) and 2-Cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (172.97 mg, 0.89 mmol, 1.20 eq). The reaction mixture was purged with nitrogen for 15 min and bis(triphenyl phosphine)palladium (II) dichloride (25.16 mg, 0.04 mmol, 0.05 eq) was added and heated under microwave at 130 OC for 1 h. The reaction mixture was concentrated and the crude obtained was purified by flash column chromatography to afford the title compound (12 mg, 0.03 mmol, 3.9%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.85 (t, J=5.64 Hz, 1H), 7.95-7.98 (m, 3H), 7.75 (d, J=9.0 Hz, 1H), 6.88 (s, 1H), 3.26-3.29 (m, 2H), 2.85-2.89 (m, 2H), 2.60 (s, 2H), 1.96-2.04 (m, 4H), 1.81-1.86 (m, 3H), 1.74-1.77 (m, 2H), 1.23-1.33 (m, 2H). m/z: 405 [M+H]+

Workup

  1. customThe reaction mixture was purged with nitrogen for 15 min
  2. temperatureheated under microwave at 130 OC for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude obtained
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-f2d17a99d1684e08af9eb1481f83e3ca
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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