Tetramethyltin → HCID 66692706, compound

HRID 2367988Notes

Reaction equation

Br[C:2]1[C:10]2[CH:9]([CH2:11][N+:12]([O-:14])=[O:13])[O:8][B:7]([OH:15])[C:6]=2[C:5]([O:16][CH2:17][CH3:18])=[CH:4][CH:3]=1.[CH3:19][Sn](C)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:17]([O:16][C:5]1[C:6]2[B:7]([OH:15])[O:8][CH:9]([CH2:11][N+:12]([O-:14])=[O:13])[C:10]=2[C:2]([CH3:19])=[CH:3][CH:4]=1)[CH3:18]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-bromo-7-ethoxy-3-(nitromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (200 mg, 0.63 mmol), tetramethylstannane (341.7 mg, 1.90 mmol) and Pd(PPh3)4 (Cat. 20 mg) in DMF (35 mL) was stirred overnight at 90° C. under N2 protection. The reaction was quenched by adding ice-water and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep-TLC to give the product (72 mg, yield 45.3%). 1H NMR (400 MHz, DMSO-d6) δ 9.00 (s, 1H), 7.23-7.21 (d, 1H), 6.83-6.81 (d, 1H), 5.77-5.75 (m, 1H), 5.27-5.24 (m, 1H), 4.50-4.44 (m, 1H), 4.08-4.03 (m, 2H), 2.25 (s, 3H), 1.33-1.29 (t, 3H).

Workup

customThe reaction was quenched
additionby adding ice-water
extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
dry with materialThe combined extracts were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by prep-TLC

Sources & evidence

ORD record: ord-21f5ef9a197a4c938852a4e752e42ff3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703742B2

Reaction notes

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