2-Thiopheneboronic acid → HCID 86620376, compound

HRID 252868Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=O)C.NC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1NC(=O)C1C=CC(OC)=CC=1.[S:42]1[CH:46]=[CH:45][CH:44]=[C:43]1B(O)O>>[N+:12]([C:6]1[C:7]([C:43]2[S:42][CH:46]=[CH:45][CH:44]=2)=[CH:8][CH:9]=[CH:10][C:5]=1[OH:4])([O-:14])=[O:13]

Participants

Reactant 3

HCID 27339602-Thiopheneboronic acid

HCID 59736724HCID 59736724, compound

HCID 59736794HCID 59736794, compound

Product 1

HCID 86620376HCID 86620376, compoundYield 32%

Conditions

Temperature: 120 °C

Procedure

Following the same procedure as in Example 44, step 2 (scheme 32) but substituting bromide 155 for bromide 328 (1.00 g, 3.85 mmol) and boronate 116 for 2-thiophene boronic acid (517 mg, 4.04 mmol) and heating at 120° C., the title compound 298 was obtained (270 mg, 32% yield). 1H NMR: (DMSO-d6) δ (ppm): 11.21 (bs, 1H), 8.07 (d, J=2.3 Hz, 1H), 7.80 (dd, J=8.6, 2.3 Hz, 1H), 7.49 (dd, J=3.5, 1.2 Hz, 1H), 7.16 (d, J=8.6 Hz, 1H), 7.11 (dd, J=5.1, 3.5 Hz, 1H), 7.07 (d, J=8.8 Hz, 1H).

Sources & evidence

ORD record: ord-8c1e8d1a0fe4479f9cbf810398980c30
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868205B2

Reaction notes

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