Dichloromethane → 6-(2,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole

HRID 529644Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:20][C:21]1[N:22]=[C:23]([Cl:39])[C:24]2[C:29](I)=[CH:28][N:27]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:25]=2[N:26]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O.O1CCOCC1>[Cl:20][C:21]1[N:22]=[C:23]([Cl:39])[C:24]2[C:29]([C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([CH3:1])[O:3][C:4]=4[CH:10]=3)=[CH:28][N:27]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:37])([CH3:36])[CH3:38])[C:25]=2[N:26]=1

Participants

Conditions

Temperature: 85 °C

Procedure

2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (1 equiv), 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), sodium carbonate (3 equiv) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (0.04 equiv) were combined in a 5:1 mixture of 1,4-dioxane and water (0.27 M). The mixture was heated to 85° C. for 1.5 h. The crude product was purified on silica gel (0-10% ethyl acetate in petroleum ether) to give an impure brown oil. The product was purified on silica gel (0-20% ethyl acetate in petroleum ether) to give the title compound (58% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.70 (d, J=8 Hz, 1H), 7.62 (s, 1H), 7.44 (m, 2H), 5.68 (s, 2H), 3.65 (m, 2H), 2.69 (s, 3H), 0.99 (m, 2H), 0.05 (s, 9H). MS (ESI) m/z 449.0 [M+1]+.

Workup

customThe crude product was purified on silica gel (0-10% ethyl acetate in petroleum ether)
customto give an impure brown oil
customThe product was purified on silica gel (0-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-3e068bab89b7445086f6a0b868a02f22
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346812B2

Reaction notes

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