Triethylamine → (E)-4-((4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)thiazol-2-yl)methyl) morpholine

HRID 2281801Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[S:5][CH:6]=1.C(N(CC)CC)C.[CH3:21][C:22]1([CH3:31])[C:26]([CH3:28])([CH3:27])[O:25][B:24]([CH:29]=[CH2:30])[O:23]1.C(OCC)(=O)C>CN(C=O)C>[CH3:27][C:26]1([CH3:28])[C:22]([CH3:31])([CH3:21])[O:23][B:24](/[CH:29]=[CH:30]/[C:2]2[N:3]=[C:4]([CH2:7][N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[S:5][CH:6]=2)[O:25]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-((4-bromothiazol-2-yl)methyl)morpholine (125 mg, 0.5 mmol) and triethylamine (0.2 mL, 1.5 mmol) in DMF (1.5 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.15 mL, 1 mmol) and Pd(Ptert-Bu3)2 (8 mg, 0.002 mmol). The mixture was heated to 120° C. under microwave irradiation for 1 h. Ethyl acetate (50 mL) was added and the solution was washed with water (2×10 mL) and brine (10 mL), dried over MgSO4 and concentrated to an orange oil (165 mg, 99%). 1H NMR (400 MHz, CDCl3) δ 7.31 (d, J=18.0 Hz, 1H), 7.19 (s, 1H), 6.40 (d, J=18.0 Hz, 1H), 3.84 (s, 2H), 3.74 (bs, 4H), 2.61 (bs, 4H), 1.29 (s, 12H); MS ESI 337.1 [M+H]+, calcd for [C16H25BN2O3S+H]+ 337.2. [α]22.8°D=−169° (c 0.42, Methanol).

Workup

washthe solution was washed with water (2×10 mL) and brine (10 mL)
dry with materialdried over MgSO4
concentrationconcentrated to an orange oil (165 mg, 99%)
custom[α]22.8°D=−169° (c 0.42, Methanol)

Sources & evidence

ORD record: ord-fef8fd758f4c497ea11a8be6f73ad13f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139563B2

Reaction notes

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