Sodium Carbonate → HCID 11992664, compound

HRID 2241046Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)=[CH:9][CH:8]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[O:39]1[CH:43]=[CH:42][CH:41]=[C:40]1B(O)O>C1COCC1>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:13](=[C:14]2[CH2:15][C:16]([CH3:22])([CH3:23])[CH2:17][C:18]([CH3:20])([CH3:21])[CH2:19]2)[C:10]2[CH:9]=[CH:8][C:7]([C:40]3[O:39][CH:43]=[CH:42][CH:41]=3)=[CH:12][CH:11]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The Suzuki procedure described for 28 was utilized using triflate 25 (150 mg, 0.319 mmol), PdCl2 (Ph3P)2 (23 mg, 0.032 mmol), 2 N aqueous Na2CO3 (1.6 mL, 3.2 mmol), 2-furanylboronic acid (179 mg, 1.6 mmol), and THF (2 mL). The mixture was heated at 120° C. for 15 min using microwave conditions. Standard work-up followed by purification gave 100 mg (81%) of the title product 30 as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.58 (d, J=8.4 Hz, 2H), 7.44 (s, 1H), 7.18-7.12 (m, 4H), 6.96 (t, J=8.8 (Hz, 2H), 6.60 (d, J=3.2 Hz, 1H), 7.45 (br s, 1H), 2.0 (s, 2H), 1.96 (s, 2H), 1.30 (s, 2H), 0.93 (s, 12H). LCMS (APCI): m/z 389 (M+H)+.

Workup

customStandard work-up followed by purification

Sources & evidence

ORD record: ord-536e85d78c3a44d38cad638972994e66
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723393B2

Reaction notes

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