Sodium Carbonate → HCID 69303364, compound

HRID 1972977Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([C:12]#[N:13])=[C:10](Br)[N:6]2[N:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH:27]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.O>[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([C:12]#[N:13])=[C:10]([C:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 4-amino-7-bromopyrrolo[2,1-f][1,2,4]triazine-6-carbonitrile (1.00 g, 4.20 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (1.95 g, 6.30 mmol) in DMF (50 mL) and DME (6.9 mL), was added sodium carbonate in water (2M, 6.3 mL). The mixture was degassed for 15 min. Dichloro[bis(diphenylphosphino)ferrocene]palladium(II) CH2Cl2 adduct (307 mg, 0.42 mmol) was added. The mixture was stirred at 80° C. under nitrogen overnight then cooled to rt. The mixture was filtered through Celite®, washing with EtOAc (100 mL) then 20% MeOH/DCM (100 mL). The filtrate was concentrated to dryness. ISCO® purification (20% EtOAc/hexane then EtOAc) afforded title compound (1.0 g, 69.4%). 1H NMR (400 MHz, DMSO-d6) δ 8.20 (s, 2H), 7.97 (s, 1H), 7.34 (s, 1H), 6.38 (t, 1H), 4.02 (d, 2H), 3.58 (t, 2H), 2.62 (t, 2H), 1.41 (s, 9H); LC-MS m/z [M+H]+ 341.2, RT 3.16 min.

Workup

customThe mixture was degassed for 15 min
temperaturethen cooled to rt
filtrationThe mixture was filtered through Celite®
washwashing with EtOAc (100 mL)
concentrationThe filtrate was concentrated to dryness
customISCO® purification (20% EtOAc/hexane

Sources & evidence

ORD record: ord-f183d02adec74d4b918f2b06c664b7f0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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