HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-(6-Amino-2'-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methylphenyl boronic acid | HCID 2733267 | — |
| Reactant | 4-(4-Amino-3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide | HCID 69586486 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | 4-(6-Amino-2'-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide | HCID 69586518 | 56% |
Reaction Steps
The procedure used in Example 1: step c was followed using 4-(4-amino-3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide ((Example 319: part d) 44 mg, 0.11 mmol), 2-methylphenylboronic acid (54 mg, 0.4 mmol), aq Na2CO3 (2M, 800 μL, 1.6 mmol), and Pd(PPh3)4 (29 mg, 0.025 mmol). Analogous workup and purification by preparative TLC yielded the title compound (24 mg, 56%). 1H-NMR (CDCl3): δ 7.97 (s, 1H), 7.76 (dd, 1H, J=2.3, 8.6 Hz), 7.67 (d, 1H, J=2.3 Hz), 7.32 (m, 2H), 7.28 (m, 1H), 7.16 (m, 1H), 6.76 (d, 1H, J=8.6 Hz), 4.11 (s, 2H), 2.58 (s, 3H), 2.13 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07109354B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-082259eb1af146999be4dd04c41ad1be |
| Source note | uspto-grants-2006_09 |