Sodium t-butoxide → HCID 69812398, compound

HRID 1809462Notes

Reaction equation

Br[C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:3]=1[CH2:4][N:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)[NH2:6].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[Si:21]([O:20][CH2:19][C:15]1[C:3]2[C:2]([CH:18]=[CH:17][CH:16]=1)=[N:6][N:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)[CH:4]=2)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (C3) in dry toluene (0.28 M) was added sodium tert-butoxide (1.5 eq.), followed by dppf (0.075 eq.) and Pd(OAc)2 (5% mol). The reaction mixture was heated to 80° C. for 35 min. After cooling down, the reaction mixture was directly loaded to a silica gel column and purified by flash column chromatography on silica (EtOAc/Petroleum ether 1:9) to yield (68%) the title compound as yellow powder. 1H NMR (300 MHz, CDCl3, 300K) δ 8.59 (1H, s), 8.07 (2H, d, J=8.7 Hz), 7.83 (2H, d, J=8.5 Hz), 7.64 (1H, d, J=8.7 Hz), 7.32-7.28 (1H, m), 7.05-7.03 (1H, m), 4.99 (2H, s), 0.96 (9H, s), 0.13 (6H, s). MS (ES+)C21H25N3OSi required: 363, found: 364 (M+H)+.

Workup

temperatureAfter cooling down
custompurified by flash column chromatography on silica (EtOAc/Petroleum ether 1:9)

Sources & evidence

ORD record: ord-c1dc09326fce44a58a72d958dad6d17c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362030B2

Reaction notes

Loading…