Cesium carbonate → HCID 86705399, compound

HRID 707485Notes

Reaction equation

[NH2:1][C:2]1[N:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][C@H:12]1[CH2:17][N:16]([CH2:18][B-](F)(F)F)[CH2:15][C@@H:14]([CH3:23])[O:13]1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[N:9]=[CH:8][C:7]([CH2:18][N:16]2[CH2:17][C@@H:12]([CH3:11])[O:13][C@@H:14]([CH3:23])[CH2:15]2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2-amino-5-bromonicotinonitrile (50 mg, 0.25 mmol), potassium (((2S,6R)-2,6-dimethylmorpholino)methyl)-trifluoroborate (219 mg, 0.51 mmol), cesium carbonate (247 mg, 0.76 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (36 mg, 0.076 mmol) and palladium(II) acetate (8.5 mg, 0.038 mmol) in dioxane (1 mL) and water (0.1 mL) was purged with nitrogen for 10 minutes, then sealed and heated at 80° C. for 15 hours. The reaction was filtered through Celite while still hot, cooled to room temperature, and diluted with water (10 mL). The resulting precipitate was filtered, washed with water (10 mL) and hexanes (10 mL), and dried under vacuum to give the title compound as a solid (57 mg, 92%). 1H NMR (400 MHz, DMSO-d6) δ 1.03 (d, J=6.3 Hz, 6H), 1.61 (t, J=10.7 Hz, 2H), 2.64 (d, J=10.7 Hz, 2H), 3.45-3.61 (m, 2H), 6.83 (s, 2H), 7.74 (d, J=2.3 Hz, 1H), 8.03-8.19 (m, 1H).

Workup

customwas purged with nitrogen for 10 minutes
customsealed
filtrationThe reaction was filtered through Celite while still hot,
temperaturecooled to room temperature
additiondiluted with water (10 mL)
filtrationThe resulting precipitate was filtered
washwashed with water (10 mL) and hexanes (10 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-aea6e34c98f048839f6dcacb6833d5d8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175010B2

Reaction notes

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